Some bridges are just bridges; others can connect you to a different world.

Bourne Bridge in Massachusetts is among the latter. Leaving the bustle of Boston, you join the Pilgrims Highway heading south-east. Soon you’re in Sagamore, on the edge of an artificial canal. Bourne Bridge allows you to cross the water with one graceful sweep, taking you off to a place that time has tinged with legend.

Cape Cod means Moby-Dick author Herman Melville and the old whaling industry. It also means lonely lighthouses, dune grass and kites caught on a warm breeze. Every place has a name like Barnstable or Wellfleet; every town feels pickled in nostalgia. “Timeless” is how one local describes it, adding: “In a world that’s constantly changing, that’s really appealing.”

To really see Cape Cod you need to drive over several days with only the loosest itinerary in mind. Driving gets you to sand-swept backstreets and unfrequented lakes.

A local’s tip leads to a whole day’s digression. What could possibly be better than that? Usually living to a routine, I decide to do the opposite for an entire long weekend and see where the mood takes me.

Not that there’s any chance of getting lost. Cape Cod isn’t particularly large and its unusual shape makes it easy to navigate. Raise your left arm and flex like a body builder. If you imagine Massachusetts as your shoulder, Cape Cod sticks out like your arm, curling around into a clenched fist. When you cross Bourne Bridge, you’re crossing at the shoulder joint. From there, visiting by car is a simple affair of following roads along the triceps and biceps, around the elbow and up a long, sandy forearm to the fist.

The fist is home to Provincetown. It marks the spot where the Pilgrims first arrived on the Mayflower in 1620, making it both the end of the road and a famous beginning.

“We are tied to the ocean,” said President John F. Kennedy, a frequent visitor to Cape Cod. “And when we go back to the sea, whether it is to sail or to watch – we are going back from whence we came.”

After crossing Bourne Bridge, I head down Route 28, determined to hit the southern shores of Cape Cod. The road is narrow and hemmed in by beech trees. I flash past shacks selling oysters and stuffed quahogs, a local variety of clam.

I notice a modest theatre staging Gypsy, a “sold out” sign plastered over the marquee as though this is a far-flung outpost of Broadway.

As the road approaches the village of Falmouth, dozens of houses emerge from the scrub. Cape Cod is characterised by its tight-knit communities, each with a different “Main Street” that resembles (to varying degrees)the manicured perfection of Disneyland. Falmouth’s Main Street, for example, features shops selling homewares made from shells and pillows stencilled with fish. I zoom past restaurants and bars on my way to Highfield Hall, an imposing Queen Anne-style mansion that commands the western extension of the street.

Highfield Hall (56 Highfield Drive) is a good first stop on Cape Cod. A plaque in the museum explains that in the 1870s, “when industrialisation and commerce began to overtake cities along the East Coast after the Civil War, residents looked to the shore as a way to escape the heat of urban summers”. Built by the family of James Madison Beebe – one of the “great merchant princes of America” – Highfield represents the earliest days of what has now become an annual pastime: decamping from Boston or New York City to frolic by the sea.

A number of American luminaries made Cape Cod their summer preference, including the illustrator Edward Gorey, whose house is preserved for curious visitors in nearby Yarmouth Port (8 Strawberry Lane).

The Kennedy family retains its famous compound in Hyannis Port, another town east of Falmouth. It remains closed off to strangers, though, so we common folk must rely on the John F. Kennedy Hyannis Museum (397 Main Street) to uncover the stories that haunt this place. The museum is interesting but it pales next to Hyannis itself: an odd, ramshackle village where ice-cream parlours line up beside a bookstore offering magazines from the 1940s and an army surplus store that sells machetes (“no service to drunks or people high on drugs! Come back sober!”). I pass on the knives, though I do buy a magazine for a sovereign. I sit down to read in the town square, where a man is yelling yoga instructions at passing tourists: “Oh, stretch out those glutes!”

Before coming to Cape Cod, I asked a friend for advice about eating and drinking here. Like many travellers, I treat holidays as an excuse to consume everything in sight and I wanted to make sure I would be consuming the good stuff.

My friend, who spent her childhood summers at Cape Cod, advised a stop in Chatham, an expensive town at the very tip of the elbow. Chatham Bars Inn (297 Shore Road) is “like Caddyshack”, she’d said, referring to the comedy movie about a snobbish country club. Curious, I stop in and snack on marinated cranberries and down a Sacred Cod cocktail (Madeira, rum, molasses and bitters), though I feel decidedly underdressed among the Ralph Lauren polos.

More casual is Chatham Pier Fish Market (45 Barcliff Avenue), where fishermen in slickers spray fish scales from the concrete with a pressure hose. At a small shack off to the side, I order a clam belly roll with loads of lemon. What’s clam belly? “Guts and all, deep-fried,” the server explains. (It tastes better than it sounds.)

Near Chatham, I meet Adeline Koscher, who lives in the area. “I can go running in cranberry bogs,” she says, when I ask her what she likes most about Cape Cod. “I can kayak any time; there’s a heron that flies over me when I do.” Another local woman, Jamie Sparrow, says something similar: “To be able to live here full-time is a privilege.” Things can get pretty slim in winter when the tourist dollars drain away, she says, but a canny person can build the sort of existence that many people only dream about.

Sparrow and her husband run a charming, Californian-style café named Sunbird (85 Route 6A, Orleans), filled with retro furniture and where menus are scrawled on brown butcher’s paper. Tucked in the crook of Cape Cod’s elbow, Sunbird also sits on a kind of threshold. “From here it gets more rough around the edges,” says Sparrow, “but also more beautiful the further up you go.”

That’s mostly because much of the land along Cape Cod’s forearm is protected as a national park, the Cape Cod National Seashore. Sandy stretches are kilometres long, surrounded by kettle ponds and woodlands. The cumulative effect is almost indescribable, though writer Henry Beston, who spent time living in a Cape Cod cottage, comes close to capturing what I see as I drive north, stopping at every lighthouse along the way: “The flux and reflux of ocean, the incomings of waves, the gatherings of birds, the pilgrimages of the peoples of the sea, winter and storm, the splendour of autumn and the holiness of spring – all these were part of the great beach.”

Anybody who drives the length of Cape Cod will eventually end up in Provincetown. But its remoteness lends it a kind of unreality – it’s often talked about in terms of a dream. The land opens out and dunes rise in rolling drifts. It feels as though you’re driving into the ocean.

The last thing you expect to see is a storybook town of quaintly coloured houses, where artists, writers, singers, dancers, gays and lesbians have carved out a glorious sanctuary. Daytripping families catch a ferry from Boston to see the spectacle. “They come to see drag queens on bikes,” says Ralph Santora, a summer local. “People who come here are open-minded. It’s a mixing bowl of all walks of life. I like the mentality behind that.”

Unlike most Cape Cod settlements, Provincetown’s main strip is called Commercial Street. Walking its length makes it clear why writer Michael Cunningham described this place as the “New Orleans of the north”. Galleries and bars vie for attention. Portuguese bakeries stack their windows with malassada – deep-fried sugared doughnuts.

At Cafe Heaven (199 Commercial Street), I dine on lobster Benedict beneath a ceiling of painted clouds. At happy hour a grand piano in The Crown & Anchor (247 Commercial Street) spills show tunes across a town barely more than two blocks wide and four kilometres long.

“There’s something strange about this town,” a woman hunched over a cocktail tells me. “It’s like you’re trapped in time!” Even the hotels can add to this feeling. Crowne Pointe Historic Inn (82 Bradford Street), for example, is a gorgeous mansion built in the late 19th century for a wealthy sea captain.

I pass most of my time in Provincetown lying on the sand at Herring Cove Beach, which is reached by walking to the end of Commercial Street and then (at high tide) wading through the West End marsh.

On my last evening in Cape Cod, I join a group of new friends for a bonfire on Race Point Beach, which faces the Atlantic. The sky streaks red and children run along the surf, pointing out seals in the fading light. Arranging the kindling, I look down the receding coastline of the cape, then east to the sea, trying to imagine the Mayflower arriving on the shore. I’m reminded of something Henry David Thoreau said about this place: “A man may stand there and put all America behind him.”

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